Tributylphosphine → HCID 88581771, compound

HRID 922320Notes

Reaction equation

HRID 922320 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH3:15][O:16]/[N:17]=[C:18](/[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)\[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]O)=[CH:23][CH:22]=1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:15][O:16]/[N:17]=[C:18](/[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)\[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetateHCID 86695770(4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol

Product 1

HCID 88581771HCID 88581771, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged 10 mL of Toluene. to the stirred solvent was added ethyl (4-hydroxyphenoxy)acetate (0.2 g, 1.030 mmol) and (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.22 g, 0.810 mmol) was added Tributyl phosphine (0.268 g, 1.32 mmol) and 1,1′(Azodicarbonyl)di-piperidene (0.33 g, 1.326 mmol). Then the reaction mixture was Stirred at RT for 3 hrs. After completion of the reaction (reaction monitored by TLC), reaction mixture was extracted with ethyl acetate. Then the organic layer was dried over anhydrous Na2SO4. Solvent was removed under reduced pressure, and the resulting crude compound was purified by column chromatography on silica gel using petroleum ether and ethyl acetate as eluent (0.13 g Yield: 28.3%): 1H NMR (300 MHz, CDCl3): δ 7.57-7.60 (m, 2H), 7.18-7.28 (m, 5H), 6.82-6.84 (d, 3H), 6.78-6.79 (d, 3H), 5.12 (s, 2H), 4.83 (s, 2H), 4.49 (s, 2H), 4.15-4.22 (m, 2H), 3.98 (s, 3H), 1.19-1.24 (t, 3H).

Workup

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction (reaction monitored by TLC), reaction mixture
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThen the organic layer was dried over anhydrous Na2SO4
  5. customSolvent was removed under reduced pressure
  6. customthe resulting crude compound was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0bc897b774ed4a09b7855914a7c07a41
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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